Journal ArticleDOI
Direct preparation of 2-deoxy-d-glucopyranosides from glucals without ferrier rearrangement
TLDR
In this paper, an efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described.Abstract:
An efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is describedread more
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Journal ArticleDOI
Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid.
TL;DR: The synthesis of a series of C9 and N5Ac modified analogs of 2,3-didehydro-N-acetyl-neuraminic acid and their inhibitory potency for the human neuraminidase 3 (NEU3) enzyme are reported.
Journal ArticleDOI
Synthetic approaches to the angucycline antibiotics: Synthesis of the C-glycosidic CD ring system
Fleur L. Andrews,David S. Larsen +1 more
TL;DR: In this article, the protected C-glycosyl substituted CD ring system of angucycline antibiotics and analogues thereof were reported, and the key step in their preparation was the C- glycosylation reaction of 5-hydroxy-1,4-dimethoxynaphthalene and a series of 1-O-acyl-2-deoxy and 1- O-acylsyl-2, 6-dideoxy sugar electrophiles promoted by boron trifluoride etherate.
Journal ArticleDOI
A Stereocontrolled Construction of 2-Deoxy-β-glycosidic Linkages via 1,2-trans-β-Glycosidation of 2-Deoxy-2-[(p-methoxyphenyl)thio] glycopyranosyl N,N,N′,N′-Tetramethylphosphoroamidates
TL;DR: In this article, a stereocontrolled synthesis of 2-deoxy-β-glycosides has been achieved by developing a salient 1,2-trans-glyco-idation method with 2-Deoxy-2-[(p-methoxyphenyl)thio] glycopyranosyl N,N,N′, N′-tetramethylphosphoroamidates as glycosyl donors.
Journal ArticleDOI
Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide
David Crich,Frank Hermann +1 more
TL;DR: In this article, the synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-β-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.
Journal ArticleDOI
C-Glycosyl juglone in angucycline synthesis: Total synthesis of galtamycinone, common aglycon of C-glycosyl naphthacenequinone-type angucyclines
TL;DR: A two-step access to C -glycosyl juglones, 16 and 17, useful intermediates toward the angucyclines, either benz[ a ]anthraquinone type or naphthacenequinone-type, has been developed based on O → C-glycoside rearrangement and (2) the regioselective cycloaddition of α-alkoxybenzyne and α-oxyfuran as mentioned in this paper.